


Stripper Problems

by mirandamyth



Series: Insurance 'verse [5]
Category: Supernatural
Genre: Alternate Universe - Human, Alternate Universe - Modern Setting, Alternate Universe- No Supernatural, Dean and Jess gang up on Sam, Domestic, Drabble, Everything is Beautiful and Nothing Hurts, Fluff, Gen, Jessica Moore Lives, and they just tease him relentlessly, but really, honestly everyone makes fun of Sam, like they're besties, ruby is the stripper, sometimes i just have sam/jess feels, they're perfect
Language: English
Status: In-Progress
Published: 2016-04-09
Updated: 2016-04-19
Packaged: 2018-05-26 01:41:27
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,046
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6218620
Author URL: https://archiveofourown.org/users/mirandamyth/pseuds/mirandamyth
Summary: <blockquote class="userstuff">
              <p>"I can't believe that, of the two of us, you're the one who married the stripper."</p>
            </blockquote>





	1. Chapter 1

"Sammy, you know I’m always in your corner, but I thought it was generally considered good manners to finalize your divorce before you start planning a marriage to someone else?" Dean leans on the kitchen island, where Sam and Jess have spread seating charts and catering menus. "I get that Ruby is a bitch, but legally, she's still your wife."

"She's still dragging out the paperwork. I married her in Vegas after three months, _and_ she left me before our first anniversary, but still feels entitled to alimony." Sam looks exasperated . "We've been legally separated for longer than we were together, hell, I've been with Jess longer than we were together."

"I know, Sam, and Jess is awesome, but is it really fair to her to plan a wedding that Ruby could easily fuck up?"

"We aren't setting a date, Jess knows that this hangs on getting Ruby out of court, and if it comes to it, we've talked about having a commitment ceremony instead, like you and Cas had. We'd just get our marriage license after Ruby realizes she can no longer pay legal fees."

"I guess you've got it all figured out, then, Sammy." Dean frowns, "Just how is she paying her lawyer?"

"Well she's back at Sheila's four nights a week," Sam grimaces, "So for all I know, she could be paying him in lap dances and blowjobs."

"I can't believe that, of the two of us, you're the one who married the stripper."

"Neither can I," Jess walks into the kitchen, drying her hair with a towel, "When he told me, I thought it was a joke."

"Sammy believed he could 'Pretty Woman' her."

"'Pretty Woman' was about a hooker, Dean." Jess laughs, "And besides, Julia Roberts is way too good to be compared to Ruby."

"Touché," Dean grins, "Are you staying for dinner, Jess? Cas'll be home in an hour, so I wanna start getting something ready."

"No, we're going to my parents' tonight. And they will probably insist we stay in the city over night." Jess sighs, "But we need to get going in the next thirty minutes, Sam." Sam stretches and heads upstairs, followed by the sound of the shower running. Jess takes the seat he'd vacated. "So, you and Cas have the house to yourselves tonight."

"Yep." Dean's half in the fridge, "I think I'm gonna make those steaks I've been saving."

"But you're gonna talk to him, right? You know, about me and Sam moving out when the lease is up?"

"That's not for another six months. Besides, me and Cas can afford this place by ourselves."

"But don't you think you could find somewhere closer to the hospital? To the garage? You could get a place near the Roadhouse, so you don't have to drive to find a bar that's not infested with frat boy assholes."

Dean winces, "Touché"

"Besides, think of all the celebration sex when you ask Cas to move in with you!"

"We've been married for two years, Jess. He's already moved in."

"With you and your brother."

"So?"

"So, it'll be fun to pick a place that's just yours. You could carry him through the threshold, all that cheesy shit." The shower shuts off upstairs, "I'm just saying, think about it. But you still should tell Cas. Maybe he has an opinion."

"Yeah, I'm sure he does." Dean sighs, "Alright, I'll talk to him."

"Try not to sound too eager, huh?" Jess grins broadly.

"Don't you have to braid Sam's hair or something, Jess? He's probably done with the blow dryer by now."

"Oh, no, we only braid his hair on Sunday nights, Dean."

"Is that before or after your Gilmore Girls binge?"

"During, of course."

"Oh, obviously." The tension in Dean's shoulders has disappeared, and he can't hold a straight face when Sam walks in. One look at his brother and the laughter just seems to burst out of him, sending Jess into a fit of giggles beside him. Sam just frowns, "You guys are jerks."

"Well, you're a bitch." Dean says at the same time Jess says "But you love us."

Sam just rolls his eyes, "C'mon Jess, we gotta get on the road." She grabs her jacket and follows him out, a chorus of 'Goodbye, Dean,' preceding the slam of the front door.

 

 


	2. Chapter 2

**Notes for the Chapter:**

> You guys win. I have literally never gotten that kind of instant response. This beat out 3/4 of my Sidelines series in less than 48 hours by hit count, hot damn. So I guess I can pull another chapter out of somewhere.

The steaks are marinating and he's got garlic parmesan potatoes roasting in the oven while he channel surfs. He cycles through sitcoms, cop shows, a Korean soccer match, and family feud reruns. The Koreans are tied 1-1, both families missed the most obvious answer, and Dean's already figured out the killer by time he hears a key in the lock. Cas come in, tie askew, feet dragging, and all Dean wants to do is put him to bed. Funny how Cas is running a sleep study but always looks exhausted.

He leaves the TV on the game and stands, "Hey babe, I've got dinner all worked out, why don't you get a shower and change?"

"Sounds great, Dean, I'm starving." Cas kisses him chastely as they cross paths, and makes his way into their bedroom.

Dean heads out to the patio to start up the grill. When he hears the shower shut off, Dean pulls the steaks off and starts steaming the broccoli. Cas comes in just as he's plating everything, his face scrunched in adorable confusion.

"Just two?"

"Yeah, Sam and Jess are visiting her parents, won't be back till tomorrow." He pulls two beers from the fridge and pops the caps with the magnetized bottle opener.

 "So the place is all ours?"

"Yeah, which is kind of what I wanted to talk to you about." Dean takes a seat at the island, pulling the chair beside him out for Cas. "So the lease on this place is up in six months."

Cas just spears a potato and nods.

"Sam and Jess are gonna get their own place when that happens. I know we could afford the rent on this place ourselves, but Jess made some good points about the benefits of maybe moving. I totally get it if you don't want to, I mean, this is home, but we could move closer to the hospital, or —" He's stopped short by the amused expression on Castiel's face.  "I say something funny?"

"I just can't tell who you're trying to talk into it, me or yourself," Cas grins widely, "maybe we could go look at some places, see what's out there. I love this house, but you are my home, Dean. This place is special because of the memories we've made here, but we can make new ones."

"So you do want to move?"

"I want to think about it. But only if we find the right space. This house is unique, full of character, it'd be hard to replace. Right now, I'd like to finish this delicious meal, curl up on the couch and watch something with with my husband. Sound good to you?"

"What are we gonna watch?" Dean's got a teasing edge to his voice, his face suggesting they won't be watching much of anything.

"Well, Sam's not here, so I figured we could get through It without any shrieking."

Dean practically giggles, the flirt on his face falling into something softer, "I fucking love you, Cas."

Castiel smiles widely, "So that's a yes?"

"Yeah, Cas, sounds like a plan."

"A better one than your porn suggestion?"

"I said no such thing!"

Cas points his fork at Dean, "Your eyebrows said it all."

 Four hours later, Dean wakes up on the couch, the DVD menu playing on repeat. Cas is tucked against his side, snoring lightly. Dean rubs his arm, "Cas, baby, come on, wake up, let's get you to bed." Cas groans and swats in Dean's general direction, but Dean sits up, jostling Cas awake enough to glare at him. "I know you're grumpy about it, but you'll sleep better in our bed."

It takes some coaxing and a few false starts, but he manages to half drag, half lead Cas to bed. All of the general unhappiness of being awoken leaves Cas once his body hits memory foam, and he wraps himself around Dean, sighing contentedly. 

 


	3. Chapter 3

She insists on driving every time they visit her parents, and he never protests — Sam loves watching Jess drive. Especially through the city in traffic. It's like watching an artist at work. She squeezes their Camry into spots even Dean might struggle with, and she curses in a steady stream of "I see you motherfuckers," "Hey dickhead, it's called a turn signal," and "Come on, asshole, fucking merge already!" That she manages to make what should be ninety minutes of stop and go traffic into seventy minutes of steady movement is just a bonus.

She always visibly relaxes when they're off the interstate; rolls the windows down and the volume up. It's times like these he catches glimpses of who she was before he knew her; when he was in Kansas and she lived here, going to Catholic school and smoking weed on the beach. The first summer they were together, she brought him here, showed him all the secret places she had spent her childhood. She had taught him how to surf, and he'd promised himself, then and there, that he was going to marry this girl.

"You're thinking something sappy, I can tell." They're less than two miles from her parent's, and Jess looks over at him, "And you need to save those dewy, sensitive eyes of yours for when we tell my dad we're engaged."

Sam just rolls his eyes and laughs as she pulls into the driveway. "You know I called and asked for his blessing, right?"

"You're slick, Sam Winchester." She kisses him across the gear shift, "Let's go."

He follows her into the house and out to the deck, where her mom is grilling tilapia, and her dad is finishing up a fresh corn salsa.

"Jessie, Sam! We weren't expecting you for another half hour."

Jess embraces first her father, then her mom. "Anything I can do to help?"

"Can you grab a bottle of white from the cooler? A Riesling, not a Moscato. I think there's a good 2010 in the kitchen cooler, but feel free to check downstairs."

"I'll be right back."

Chuck Moore invites Sam to take a seat, "Jessie says law school is going well."

"Yes, sir. It's hard work, but it's what I've always wanted."

"One more year left, right?"

"That's what I keep telling myself — I've got an internship this summer with the ACLU, and another lined up in the fall with the public defense office."

Jess interrupts with the wine, handing out glasses and setting the table. Sam and Jess are sent in for guacamole, lettuce, tomatoes, and sour cream. The tortillas have been on the grill with the fish and are the perfect temperature for a well wrapped taco. They watch the sun set over dessert, mango sorbet with fresh strawberries, and Sam raises his glass for a toast, "I want to thank you two, for always making me feel welcome, and I'm so glad that I'm marrying your daughter."

While Jess's mother gushes over the ring, the proposal, Chuck just claps Sam on the shoulder, "Welcome to the family, son."

Sam beams, "Thanks, Chuck."

It's not long before Maggie makes her way over to Sam. Misty eyed and smiling, she wraps her arms around him, "You take care of my little girl."

"For as long as I'm alive." Sam promises. She squeezes him once more before releasing him and steps back, "Well, let's get this cleaned up."

The four of them make quick work of storing the leftovers and loading up the dishwasher, before the older two excuse themselves for the night. Jess settles in next to Sam on her parents' couch and challenges him to Mario Kart. She's aggressive even when the driving is only virtual. She slams him off the track more times than he can count, and trash talks the computer. Every time she wins, she thrusts her fists in the air in triumph. Before long she leads Sam back to her childhood bedroom, and they manage to find a comfortable way to share the twin bed.

**Notes for the Chapter:**

> Another chapter! Of just Sam and Jess? You got it!

**Author's Note:**

> I stole the prompt from Belated by ellieelephant  
> "Buddy, you know I’m always in your corner, but I thought it was generally considered good manners to finalize your divorce before you start planning a marriage to someone else?"
> 
> Maybe more later, idk.


End file.
